US4632959A - Modified polyolefin composition - Google Patents
Modified polyolefin composition Download PDFInfo
- Publication number
- US4632959A US4632959A US06/651,894 US65189484A US4632959A US 4632959 A US4632959 A US 4632959A US 65189484 A US65189484 A US 65189484A US 4632959 A US4632959 A US 4632959A
- Authority
- US
- United States
- Prior art keywords
- copolymer
- ethylene
- composition
- modified
- polyolefin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 229920000098 polyolefin Polymers 0.000 title claims abstract description 156
- 239000000203 mixture Substances 0.000 title claims abstract description 88
- 229920000642 polymer Polymers 0.000 claims abstract description 89
- 229920001169 thermoplastic Polymers 0.000 claims abstract description 27
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 19
- 239000004593 Epoxy Substances 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 230000009477 glass transition Effects 0.000 claims abstract description 8
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000000853 adhesive Substances 0.000 claims abstract description 3
- 230000001070 adhesive effect Effects 0.000 claims abstract description 3
- 238000002425 crystallisation Methods 0.000 claims abstract 4
- 230000008025 crystallization Effects 0.000 claims abstract 4
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 101
- 229920001577 copolymer Polymers 0.000 claims description 98
- -1 styrene hydrocarbons Chemical class 0.000 claims description 88
- 239000005977 Ethylene Substances 0.000 claims description 72
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 70
- WSSSPWUEQFSQQG-UHFFFAOYSA-N dimethylbutene Natural products CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 claims description 36
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 25
- 229920002367 Polyisobutene Polymers 0.000 claims description 21
- 239000002245 particle Substances 0.000 claims description 18
- 239000000178 monomer Substances 0.000 claims description 14
- 229920001038 ethylene copolymer Polymers 0.000 claims description 13
- 239000004711 α-olefin Substances 0.000 claims description 13
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 10
- 239000004215 Carbon black (E152) Substances 0.000 claims description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- AFFLGGQVNFXPEV-UHFFFAOYSA-N n-decene Natural products CCCCCCCCC=C AFFLGGQVNFXPEV-UHFFFAOYSA-N 0.000 claims description 7
- 229920000089 Cyclic olefin copolymer Polymers 0.000 claims description 6
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- LIKMAJRDDDTEIG-UHFFFAOYSA-N n-hexene Natural products CCCCC=C LIKMAJRDDDTEIG-UHFFFAOYSA-N 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 229920002554 vinyl polymer Polymers 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N alpha-Methyl-n-butyl acrylate Natural products CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 5
- 239000004716 Ethylene/acrylic acid copolymer Substances 0.000 claims description 4
- CGPRUXZTHGTMKW-UHFFFAOYSA-N ethene;ethyl prop-2-enoate Chemical compound C=C.CCOC(=O)C=C CGPRUXZTHGTMKW-UHFFFAOYSA-N 0.000 claims description 4
- YYXLGGIKSIZHSF-UHFFFAOYSA-N ethene;furan-2,5-dione Chemical compound C=C.O=C1OC(=O)C=C1 YYXLGGIKSIZHSF-UHFFFAOYSA-N 0.000 claims description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 4
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003999 initiator Substances 0.000 claims description 4
- 239000011159 matrix material Substances 0.000 claims description 4
- 229920003145 methacrylic acid copolymer Polymers 0.000 claims description 4
- 229940117841 methacrylic acid copolymer Drugs 0.000 claims description 4
- CCCMONHAUSKTEQ-UHFFFAOYSA-N octadecene Natural products CCCCCCCCCCCCCCCCC=C CCCMONHAUSKTEQ-UHFFFAOYSA-N 0.000 claims description 4
- 229920001748 polybutylene Polymers 0.000 claims description 4
- JZHGRUMIRATHIU-UHFFFAOYSA-N 1-ethenyl-3-methylbenzene Chemical compound CC1=CC=CC(C=C)=C1 JZHGRUMIRATHIU-UHFFFAOYSA-N 0.000 claims description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 3
- 239000006096 absorbing agent Substances 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- 239000003963 antioxidant agent Substances 0.000 claims description 2
- 239000002216 antistatic agent Substances 0.000 claims description 2
- 239000000975 dye Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 239000003063 flame retardant Substances 0.000 claims description 2
- 229920000578 graft copolymer Polymers 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 239000002667 nucleating agent Substances 0.000 claims description 2
- 239000000049 pigment Substances 0.000 claims description 2
- 239000004014 plasticizer Substances 0.000 claims description 2
- 239000012748 slip agent Substances 0.000 claims description 2
- 229920001112 grafted polyolefin Polymers 0.000 claims 3
- 230000000996 additive effect Effects 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract description 16
- 239000010410 layer Substances 0.000 description 71
- 238000002156 mixing Methods 0.000 description 42
- 229920000573 polyethylene Polymers 0.000 description 36
- 239000000047 product Substances 0.000 description 34
- 239000004698 Polyethylene Substances 0.000 description 33
- 238000000034 method Methods 0.000 description 33
- 229920001971 elastomer Polymers 0.000 description 31
- 239000000806 elastomer Substances 0.000 description 27
- 230000000052 comparative effect Effects 0.000 description 21
- 239000004417 polycarbonate Substances 0.000 description 21
- 229920000515 polycarbonate Polymers 0.000 description 21
- 239000000463 material Substances 0.000 description 20
- 239000004793 Polystyrene Substances 0.000 description 19
- 229920002223 polystyrene Polymers 0.000 description 19
- 239000011229 interlayer Substances 0.000 description 15
- 229920000131 polyvinylidene Polymers 0.000 description 13
- 239000003607 modifier Substances 0.000 description 12
- 229920001155 polypropylene Polymers 0.000 description 12
- 239000004743 Polypropylene Substances 0.000 description 8
- 125000000524 functional group Chemical group 0.000 description 7
- 229920005669 high impact polystyrene Polymers 0.000 description 7
- 239000004797 high-impact polystyrene Substances 0.000 description 7
- 229920001179 medium density polyethylene Polymers 0.000 description 7
- 239000004701 medium-density polyethylene Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 238000005227 gel permeation chromatography Methods 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 6
- 229920000139 polyethylene terephthalate Polymers 0.000 description 6
- 239000005020 polyethylene terephthalate Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 5
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 5
- 239000012790 adhesive layer Substances 0.000 description 5
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 239000005033 polyvinylidene chloride Substances 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 4
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 4
- 125000000962 organic group Chemical group 0.000 description 4
- 229920006380 polyphenylene oxide Polymers 0.000 description 4
- 239000005060 rubber Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 229920001875 Ebonite Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000004677 Nylon Substances 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 229920001195 polyisoprene Polymers 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- GQEZCXVZFLOKMC-UHFFFAOYSA-N 1-hexadecene Chemical compound CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 2
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 2
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- OCXPJMSKLNNYLE-UHFFFAOYSA-N 2-prop-2-enylbutanedioic acid Chemical compound OC(=O)CC(C(O)=O)CC=C OCXPJMSKLNNYLE-UHFFFAOYSA-N 0.000 description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 2
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 229920002292 Nylon 6 Polymers 0.000 description 2
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 2
- 239000004952 Polyamide Substances 0.000 description 2
- 238000002441 X-ray diffraction Methods 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- NIDNOXCRFUCAKQ-UHFFFAOYSA-N bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2C(O)=O NIDNOXCRFUCAKQ-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Chemical group 0.000 description 2
- 229920005549 butyl rubber Polymers 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 2
- 229940018557 citraconic acid Drugs 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000004567 concrete Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000010559 graft polymerization reaction Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- VAMFXQBUQXONLZ-UHFFFAOYSA-N n-alpha-eicosene Natural products CCCCCCCCCCCCCCCCCCC=C VAMFXQBUQXONLZ-UHFFFAOYSA-N 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
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- 239000002244 precipitate Substances 0.000 description 2
- 239000002243 precursor Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
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- JIYNFFGKZCOPKN-UHFFFAOYSA-N sbb061129 Chemical compound O=C1OC(=O)C2C1C1C=C(C)C2C1 JIYNFFGKZCOPKN-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000011282 treatment Methods 0.000 description 2
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 2
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- 239000002023 wood Substances 0.000 description 2
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- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- KTZVZZJJVJQZHV-UHFFFAOYSA-N 1-chloro-4-ethenylbenzene Chemical compound ClC1=CC=C(C=C)C=C1 KTZVZZJJVJQZHV-UHFFFAOYSA-N 0.000 description 1
- 229940106006 1-eicosene Drugs 0.000 description 1
- FIKTURVKRGQNQD-UHFFFAOYSA-N 1-eicosene Natural products CCCCCCCCCCCCCCCCCC=CC(O)=O FIKTURVKRGQNQD-UHFFFAOYSA-N 0.000 description 1
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- YBHWIVKIQYJYOH-UHFFFAOYSA-N 1-ethenyl-2-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC=C1C=C YBHWIVKIQYJYOH-UHFFFAOYSA-N 0.000 description 1
- XHUZSRRCICJJCN-UHFFFAOYSA-N 1-ethenyl-3-ethylbenzene Chemical compound CCC1=CC=CC(C=C)=C1 XHUZSRRCICJJCN-UHFFFAOYSA-N 0.000 description 1
- BYYLJVQCWRRFMP-UHFFFAOYSA-N 1-ethenyl-3-propan-2-ylbenzene Chemical compound CC(C)C1=CC=CC(C=C)=C1 BYYLJVQCWRRFMP-UHFFFAOYSA-N 0.000 description 1
- WHFHDVDXYKOSKI-UHFFFAOYSA-N 1-ethenyl-4-ethylbenzene Chemical compound CCC1=CC=C(C=C)C=C1 WHFHDVDXYKOSKI-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F255/00—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00
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- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
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- C08F255/02—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms
- C08F255/026—Macromolecular compounds obtained by polymerising monomers on to polymers of hydrocarbons as defined in group C08F10/00 on to polymers of olefins having two or three carbon atoms on to ethylene-vinylester copolymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
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- C08L23/18—Homopolymers or copolymers of hydrocarbons having four or more carbon atoms
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
- C08L2666/04—Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
Definitions
- modified polyolefin denotes a polymer having an olefin as a main component, which has been modified by introducing a functional group in accordance with such techniques as random copolymerization, block copolymerization, graft copolymerization, halogenation or saponification.
- an epoxy group is introduced in order to improve the adhesion or heat resistance of polyolefins
- a halogen-containing group is introduced into polyolefins in order to improve their weatherability, water resistance and chemical resistance.
- the polyolefins intrinsically have poor adhesion to polar materials such a metals, concrete, polar resins, wood, etc. Since in many cases the introduction of such functional groups also improves the adhesion of the polyolefins to such polar materials, the modified polyolefins are used as laminates with these materials, or as intermediate adhesive layers of laminates of these polar materials. They are also used as a paint, etc. for surface protection of these polar materials.
- modified polyolefins have the defect that their adhesiveness is low depending upon the type of modification and the polar materials to which they are bonded, and they easily peel off under severe use conditions or under certain bonding conditions.
- Japanese Laid-Open Patent Publication No. 127613/1981 discloses an easily peelable heat sealing material composed of a blend of a propylene polymer and a modified ethylene polymer obtained by grafting 40 to 95% by weight of an ethylene polymer with 60 to 5% by weight of an aromatic vinyl monomer. This resin composition positively utilizes the aforesaid easy peelability of the modified polyolefins.
- thermoplastic polymer selected from the group consisting of
- thermoplastic polymers having a flexural modulus of less than 1000 kg/cm 2 , a glass transition temperature (Tg) of not higher than 0° C. and a weight average molecular weight (Mw) of at least 400,000, and
- (B-2) polar non-olefinic thermoplastic polymers or ethylenic polymers having a flexural modulus of at least 1000 kg/cm 2 and an adhesion strength, with respect to the modified polyolefin (A), of not more than 200 g/cm.
- the modified polyolefin (A) as a main component of the modified polyolefin composition of this invention is a polymer composed mainly of an ⁇ -olefin.
- the ⁇ -olefin as a base may be an ⁇ -olefin which may have a branched chain, such as ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 4-methyl-1-pentene, 3-methyl-1-pentene, 1-octene, 1-decene, 1-dodecene, 1-hexadecene, 1-octadecene, or 1-eicosene.
- Such as olefin may generally have 2 to 20, preferably 2 to 16, more preferably 2 to 10 carbon atoms.
- the modified polyolefin (A) can be prepared by introducing a functional group by such a technique as described hereinbelow into a polyolefin prepared by homopolymerization of the above-exemplified ⁇ -olefin or the copolymerization of two or more such ⁇ -olefins. Or it can be prepared by copolymerizing the aforesaid ⁇ -olefin with a monomer containing a functional group or a precursor group easily convertible to a functional group.
- polystyrene-type polymers including polyethylene, ethylene/ ⁇ -olefin copolymers (with an ethylene content of at least 75 mole%) such as an ethylene/propylene copolymer, an ethylene/1-butene copolymer, an ethylene/4-methyl-1-pentene copolymer, an ethylene/1-hexene copolymer, an ethylene/1-octene copolymer and an ethylene/1-decene copolymer, and ethylene/vinyl monomer copolymers (the total vinyl monomer content being not more than 15 mole%) such as an ethylene/vinyl acetate copolymer, an ethylene/ethyl acrylate copolymer, an ethylene/acrylic acid copolymer, a partially neutralized salt of an ethylene/acrylic acid copolymer, an ethylene/methacrylic acid copolymer, a partially neutralized salt of an ethylene-type polymers (with an ethylene content of at least
- polypropylene propylene/ ⁇ -olefin copolymers (with a propylene content of at least 60 mole%) such as a propylene/ethylene copolymer, a propylene/1-butene copolymer, a propylene/1-hexene copolymer and a propylene/4-methyl-1-pentene copolymer, polybutene-1, 1-butene/ ⁇ -olefin copolymers (with a 1-butene content of at least 60 mole%) such as a 1-butene/ethylene copolymer, a 1-butene/propylene copolymer, a 1-butene/4-methyl-1-pentene copolymer and a 1-butene/1-hexene copolymer, poly-4-methyl-1-pentene, and 4-methyl-1-pentene/ ⁇ -olefin copolymers (with a 4-methyl-1-pentene content of at least 80 mole%
- grafted products of the aforesaid ⁇ -olefin copolymers or ethylene/vinyl monomer copolymers and at least one unsaturated carboxylic acid are also useful as the base polyolefin used in this invention.
- the grafted polymers contain not more than 3 mole%, preferably not more than 1 mole%, more preferably not more than 0.5 mole%, of the unsaturated carboxylic acid).
- the unsaturated carboxylic acid is selected from the group consisting of unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, fumaric acid, itaconic acid, citraconic acid, allylsuccinic acid, mesaconic acid, glutaconic acid, Nadic acid, methyl Nadic acid, tetrahydrophthalic acid and methylhexahydrophthalic acid, and unsaturated dicarboxylic acid anhydrides such as maleic anhydride, itaconic anhydride, citraconic anhydride, allylsuccinic anhydride, glutaconic anhydride, Nadic anhydride, methyl Nadic anhydride, tetrahydrophthalic anhydride and methyltetrahydrophthalic anhydride.
- These polymers are especially useful when in the production of a laminated article, a polymer having barrier properties, such as a polyamide or an ethylene/vinyl alcohol copolymer, is used as one layer.
- these polyolefins have an intrinsic viscosity [ ⁇ ], measured in decalin at 135° C., of 0.5 to 15 dl/g, a crystallinity, measured by an X-ray diffraction method under the conditions set forth in ASTM D-618, of at least 20%, and a molecular weight distribution [weight average molecular weight (Mw)/number average molecular weight (Mn)], measured by the GPC method in o-dichlorobenzene as a solvent at 135° C., of from 1 to 30.
- ⁇ intrinsic viscosity
- Mw weight average molecular weight
- Mn numberber average molecular weight
- modified polyolefins which can be used as the modified polyolefin (A) in the composition of this invention are described below in greater detail.
- the styrene-type hydrocarbon-modified polyolefins can usually be produced by graft-polymerizing styrene-type hydrocarbons to such polyolefins as exemplified above.
- the styrene-type hydrocarbons preferably include those represented by the following formula ##STR1## wherein R 1 represents a hydrogen, or an alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms, and R 2 represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 6 carbon atoms, preferably 1 to 4 carbon atoms.
- styrene-type hydrocarbons are styrene, alpha-methylstyrene, o-chlorostyrene, p-chlorostyrene, o-methylstyrene, m-methylstyrene, p-methylstyrene, m-ethylstyrene, p-ethylstyrene, o-isopropylstyrene, m-isopropylstyrene and p-isopropylstyrene. Of these, styrene, m-methylstyrene and p-methylstyrene are preferred.
- styrene-type hydrocarbons may be graft-polymerized singly or as a mixture of two or more.
- the convenient proportion of the styrene-type hydrocarbon to be graft-polymerized is generally 10 -5 to 5 ⁇ 10 -3 gram-equivalent, preferably 2 ⁇ 10 -5 to 2 ⁇ 10 -3 gram-equivalent, more preferably 5 ⁇ 10 -5 to 1.5 ⁇ 10 -3 gram-equivalent, per gram of the polyolefin.
- Grafting of the styrene-type hydrocarbon to the polyolefin can be carried out by reacting the polyolefin and the styrene-type hydrocarbon in the heat-molten state or in the form of a solution in the presence of a radical initiator [such as benzoyl peroxide, dicumyl peroxide, di-tert.-butyl peroxide, 2,5-dimethyl-2,5-di(tert.-butylperoxy)hexane-3, ⁇ , ⁇ '-bis(tert.-butylperoxyisopropyl)benzene, or 2,5-dimethyl-2,5-di(tert.-butylperoxy)hexyne-3] by a method known per se (for example, the method described in Japanese Laid-Open Patent Publication No. 16864/1983) or by the method described in Japanese Laid-Open Patent Publication No. 15467/1984.
- a radical initiator such as be
- the unsaturated epoxy compounds-modified polyolefins can be produced by copolymerizing at least one of the above-exemplified olefins with at least one unsaturated epoxy compound, or by graft-polymerizing an unsaturated epoxy compound to the aforesaid polyolefin.
- the former is described, for example, in Japanese Patent Publication No. 27527/1971 or Japanese Laid-Open Patent Publication No. 11388/1973.
- the latter is described, for example, in Japanese Patent Publication No. 31276/1977.
- unsaturated epoxy compound-modified polyolefins obtained by the latter graft-polymerizing method have good adhesion and are preferred.
- the graft-polymerization of the unsaturated epoxy compound to the polyolefin can be carried out in the presence of a radical initiator (such as benzoyl peroxide and dicumyl peroxide) in an alkyl aromatic hydrocarbon solvent such as toluene or xylene at a temperature of usually 100° to 160° C.
- a radical initiator such as benzoyl peroxide and dicumyl peroxide
- the unsaturated epoxy compound used in the production of the modified polyolefin is a compound having at least one ethylenically unsaturated bond and at least one epoxy group per molecule.
- Specific examples include glycidyl esters of unsaturated carboxylic acids such as glycidyl acrylate, glycidyl methacrylate, a mono- or di-glycidyl ester of itaconic acid, a mono- or di-glycidyl ester of citraconic acid, a mono-, di- or tri-glycidyl ester of butenetricarboxylic acid, a mono- or di-glycidyl ester of endo-cis-bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid (Nadic Acid, a trade name), a mono- or di-glycidyl ester of endo-cis-bicyclo-[2.2.1]hept-5-ene-2-methyl-
- the proportion of the unsaturated epoxy compound to be polymerized is desirably such that the resulting modified polyolefin contains generally 10 -6 to 10 -3 gram-equivalent, preferably 10 -5 to 5 ⁇ 10 -4 gram-equivalent, more preferably 2 ⁇ 10 -5 to 4 ⁇ 10 -4 gram-equivalent, of epoxy groups per gram of the modified polyolefin.
- polyolefin modified with unsaturated silane compounds can usually be prepared by graft-polymerizing unsaturated silane compounds to polyolefins.
- the unsaturated silane compounds used as modifying agents include those represented by the following formula ##STR2## wherein R 3 and R 4 are identical or different and each represents a hydrocarbon group which has an ethylenically unsaturated bond and which may optionally contain an oxygen atom; R 5 represents a halogen atom or an organic group not containing an ethylenically unsaturated bond; and Y 1 , Y 2 and Y 3 are identical or different and each represents an organic group capable of being changed to a hydroxyl group by hydrolysis.
- the "hydrocarbon group which has an ethylenically unsaturated bond and which may optionally contain an oxygen atom" represented by R 3 and R 4 is a group having reactivity with the radical site generated in the polyolefin during the graft polymerization, and includes, for example, vinyl, allyl, butenyl, cyclohexenyl and cyclopentadienyl groups. Hydrocarbon groups having an ethylenically unsaturated bond at the terminal are preferred. Other suitable examples include groups containing an ester residue derived from a carboxylic acid having an ethylenically unsaturated bond at the terminal, such as ##STR3## Of these, a vinyl group is especially preferred.
- the "halogen atom” represented by R 5 is preferably chlorine or bromine.
- Examples of the "organic group not containing an ethylenically unsaturated bond” include monovalent hydrocarbon groups, for example alkyl groups such as methyl, ethyl, propyl, butyl, hexyl, tetradecyl or octadecyl, aryl groups such as phenyl or tolyl, aralkyl groups such as benzyl or phenethyl, and halogen-substituted derivatives of these hydrocarbon groups such as chloromethyl, chloroethyl and chlorophenyl.
- Examples of the hydrolyzable organic group represented by Y 1 , Y 2 and Y 3 include alkoxy groups or alkoxyalkoxy groups, such as methoxy, ethoxy, butoxy and methoxyethoxy; acyloxy groups such as formyloxy, acetoxy or propionoxy; oxime groups such as --ON ⁇ C(CH 3 ) 2 , --ON ⁇ CHC 3 H 7 and --ON ⁇ C(C 6 H 5 ) 2 ; and alkylamino or arylamino groups, such as --NHCH 3 , --NHC 2 H 5 and --NH(C 6 H 5 ).
- unsaturated silane compounds which can be used as modifying agents include vinyltrimethoxysilane, vinyltriethoxysilane and vinyltris(2-methoxyethoxy)silane.
- Modification of polyolefins using such unsaturated silane compounds can be carried out by methods known per se, for example in accordance with the methods described in Japanese Patent Publication No. 1711/1973, and Japanese Laid-Open Patent Publication No. 28386/1979.
- a radical generator such as dicumyl peroxide, tert.-butyl perpivalate, benzoyl peroxide, 2,5-dimethyl-2,5-di(tert.-butylperoxy)hexene-3 or 2,5-dimethyl-2,5-di(tert.-butylperoxy)hexyne-3 under heat or by mixing them in a hydrocarbon solvent at 80° to 200° C.
- the proportion of the unsaturated silane compound to be grafted is generally 10 -6 to 10 -3 gram-equivalent, preferably 10 -5 to 5 ⁇ 10 -4 gram-equivalent, more preferably 5 ⁇ 10 -5 to 3 ⁇ 10 -4 gram-equivalent, per gram of the modified polyolefin formed.
- the halogenated polyolefins can be prepared in a customary manner, for example by contacting a solution or aqueous dispersion of the polyolefin with a halogenating agent such as chlorine, bromine, N-chlorosuccinimide or N-bromosuccinimide.
- a halogenating agent such as chlorine, bromine, N-chlorosuccinimide or N-bromosuccinimide.
- Aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons and halogenated hydrocarbons may be used as solvents for the polyolefin.
- Halogenated hydrocarbons such as chlorobenzene or trichloroethane are preferred.
- the concentration of the polyolefin in the solution or aqueous dispersion is not critical, but usually it is conveniently about 0.1 to 50% by weight.
- the halogenation may generally be carried out at a temperature of about 0° to about 200° C. for about 1 to about 20 hours.
- halogenated polyolefin examples include chlorinated polyethylene, chlorinated ethylene/propylene copolymer, chlorinated ethylene/1-butene copolymer, chlorinated ethylene/1-butene copolymer, chlorinated ethylene/4-methyl-1-pentene copolymer, chlorinated ethylene/1-octene copolymer, chlorinated polypropylene, chlorinated propylene/ethylene copolymer, and chlorinated propylene/1-butene copolymer.
- chlorinated polybutene-1 chlorinated 1-butene/ethylene copolymer, chlorinated 1-butene/propylene copolymer, chlorinated poly(4-methyl-1-pentene), chlorinated 4-methyl-1-pentene/1-decene copolymer, brominated ethylene/propylene/diene rubber, brominated polypropylene, brominated polybutene-1 and brominated poly(4-methyl-1-pentene).
- chlorinated polyolefins are preferred.
- the halogen content of the halogenated polyolefin that can be used in the composition of this invention is desirably 0.3 ⁇ 10 -5 to 2 ⁇ 10 -2 gram-equivalent, preferably 0.84 ⁇ 10 -4 to 10 -2 gram-equivalent, more preferably 2 ⁇ 10 -4 to 7 ⁇ 10 -3 gram-equivalent, per gram of the halogenated polyolefin.
- the hydroxyl group-containing polyolefins can be prepared, for example, by copolymerizing the olefin with a monomer having a hydroxyl group or a precursor group capable of being changed to a hydroxyl group or by grafting the aforesaid monomer to the polyolefin.
- a monomer having a hydroxyl group or a precursor group capable of being changed to a hydroxyl group or by grafting the aforesaid monomer to the polyolefin is a polymer obtained by saponifying an ethylene/vinyl acetate copolymer having an ethylene content of 30 to 99 mole% to a saponification degree of 10 to 100%.
- Such hydroxyl group-containing polyolefins may contain the hydroxyl group in an amount of generally 3 ⁇ 10 -5 to 10 -2 gram-equivalent, preferably 5 ⁇ 10 -5 to 8 ⁇ 10 -3 gram-equivalent, more preferably 10 -4 to 6 ⁇ 10 -3 gram-equivalent, per gram of the polymer.
- the modified polyolefin (A) selected from the group consisting of the styrene-type hydrocarbon-modified polyolefins (A-1), the unsaturated epoxy compound-modified polyolefins (A-2), the unsaturated silane compound-modified polyolefins (A-3), the halogenated polyolefins (A-4), and the hydroxyl group-containing polyolefins (A-5) should have an intrinsic viscosity [ ⁇ ] of 0.5 to 10 dl/g, preferably 0.8 to 7 dl/g, more preferably 1.0 to 5 dl/g, in order to provide a modified polyolefin composition having excellent adhesion as contemplated by the present invention.
- the "intrinsic viscosity [ ⁇ ]" is a value measured at 135° C. in decalin as a solvent.
- the modified polyolefin (a) should have a crystallinity of at least 20%.
- crystallinity denotes a value measured by an X-ray diffraction method using a sample prepared by the method described in ASTM D-618.
- the modified polyolefin can have a crystallinity of preferably at least 25%, more preferably at least 35%.
- the modified polyolefin used in this invention has a relatively narrow molecular weight distribution.
- the molecular weight distribution is expressed by the ratio of its weight average molecular weight (Mw) to its number average molecular weight (Mn), i.e. (Mw/Mn).
- Mw/Mn is generally from 1 to 30, preferably from 1 to 20, and more preferably from 1 to 15.
- the weight average molecular weight Mw and the number average molecular weight Mn of the polymer are measured by the following procedure using gel permeation chromatography (GPC).
- 150 mg of the polymer, 100 ml of o-dichlorobenzene as a solvent and 0.04 g of 2,6-di-tert.-butyl-p-cresol as a stabilizer are mixed.
- the mixture is heated to 140° C. to dissolve the polymer.
- the solution is passed through a 0.2-micron filter to remove insoluble materials such as dirt and dust at 140° C.
- the measurement is carried out by using a GPC measuring device (Model LC-GPC 150C of Waters Associates Inc.) and a column (Type TSKGMH6 of Toyo Soda Manufacturing Co., Ltd.) at a temperature of 135° C. and a flow rate of 1.0 ml/min.
- the numerical value is converted to a value based on polystyrene.
- thermoplastic polymer (B) to be blended with the modified polyolefin (A) may be (B-1) a thermoplastic polymer having a flexural modulus of at least 1000 kg/cm 2 . These polymers will be described below in detail.
- the "flexural modulus” is a value measured by the method described in ASTM D-790.
- thermoplastic polymers used in this invention should have a glass transition temperature (Tg) of not more than 0° C., preferably -150° to 0° C., more preferably -130° to -20° C.
- Tg glass transition temperature
- thermoplastic polymers should have a weight average molecular weight (Mw) of at least 400,000, preferably as high as at least 500,000, when it is measured by the GPC method as described hereinabove.
- Mw weight average molecular weight
- the above-mentioned soft polymer having a weight average molecular weight (Mw) of less than 400,000 is blended with the modified polyolefin (A), an effect of increasing the adhesion strength to such a high level as is observed in the present invention cannot be obtained.
- the soft thermoplastic polymers (B-1) are rubbery elastomers having a flexural modulus of not more than 100 kg/cm 2 , particularly not more than 50 kg/cm 2 .
- soft thermoplastic polymers which can be used in this invention include polyisobutylene, polyhexene-1, polyoctene-1, ethylene/propylene copolymer rubber, ethylene/propylene/diene terpolymer, ethylene/1-butene copolymer rubber, propylene/ethylene copolymer rubber, 1-butene/ethylene copolymer rubber, polydecene-1, polydodecene-1, polyisoprene, butyl rubber and silicone rubber.
- these soft polymers have a crystallinity of generally not more than 30%, preferably not more than 25%, more preferably not more than 20%.
- their molecular weight distribution (Mw/Mn) is 1 to 30, preferably 1 to 20, more preferably 1 to 15.
- soft thermoplastic polymers (B-1) which can be used especially advantageously in this invention include polyisobutylene, polyisoprene, polyhexene-1, polyoctene-1, polydecene-1, ethylene/propylene copolymer rubber, ethylene/propylene/diene terpolymer, and butyl rubber.
- polymers are selected from the group consisting of polar non-olefinic thermoplastic polymers (B-2-A) and ethylenic polymers (B-2-B) having an adhesion strength, with respect to the modified polyolefin to be blended, of not more than 200 g/cm, preferably not more than 80 g/cm, more preferably not more than 50 g/cm.
- non-olefinic means that the polymers do not substantially contain an olefin unit.
- ethylenic polymers means a homopolymer of ethylene or copolymers of ethylene having at least 50 mole% of an ethylene unit.
- the "adhesion strength”, used in the present specification and the appended claims, is measured by a T-peel testing method (pulling speed 100 mm/min., 23° C.) on a testing sample, 1 cm wide, cut off from a two-layer sheet (each layer having a thickness of 100 microns) which is obtained by co-extruding the two polymer components from two extruders into one T-die.
- polar means the inclusion within molecular chains of a structural unit composed of chemical bonds other than C--H and C--C bonds. It should be understood that an aromatic ring skeleton is included within the definition of "polar".
- polystyrene examples include polystyrene; polyamides such as nylon-6, nylon-10, nylon-11, nylon-12, 6,6-nylon and 6,10-nylon; polyesters such as polyethylene terephthalate, polybutylene terephthalate, polyethylene terephthalate isophthalate, bisphenol A/terephthalic acid copolycondensate and ethylene glycol/cyclohexane dimethanol/terephthalic acid copolycondensate; polycarbonates such as polycarbonate of bisphenol A, polycarbonate of bisphenol F and polycarbonate of bisphenol AD; polyphenylene oxide polymers such as polyphenylene oxide, modified polyphenylene oxide and grafted polyphenylene oxide; acrylic polymers such as polymethyl methacrylate, polybutyl methacrylate, methyl methacrylate/butyl methacrylate copolymer, polyglycidyl methacrylate and polymethyl acrylate; styrene-type polymers such as polyst
- these polymers may have a flexural modulus of at least 1,500 kg/cm 2 , preferably 2,000 to 50,000 kg/cm 2 .
- the polymers (B-1) and (B-2) may be used singly. Alternatively, at least two species selected from each of the polymers (B-1) or (B-2) may be used, or a combination of at least one species from the polymers (B-1) and at least one species from the polymers (B-2) may be used.
- the polymer (B) may be present as a dispersed phase in a matrix of the modified polyolefin (A) in the composition of this invention.
- the dispersed phase may be composed of a mixture of the two or more polymers, or each dispersed phase may be composed of a single polymer.
- the two or more polymers (B) are mixed in advance and blended with the modified polyolefin (A) by methods to be described below.
- composition of this invention can be prepared by blending and dispersing the thermoplastic polymer (B) with and in the modified polyolefin (A).
- the blending proportions of the modified polyolefin (A) and the polymer (B) may be within the following ranges provided that the total amount of (A) and (B) is 100 parts by weight.
- the polymer (B) may generally form a dispersed phase of fine particles in the matrix of the modified polyolefin (A).
- the particle diameter of the dispersed phase of the polymer (B), as its average circle equivalent diameter (d) is generally in the range of 0.1 to 5 microns, preferably 0.3 to 4 microns, more preferably 0.5 to 3 microns.
- the "average circle equivalent diameter [d]" is an index introduced because the particles in the dispersed phase are not always completely spherical. It is determined in accordance with the following equation. ##EQU1## wherein n is the number of particles of the polymer (B) observed microscopically on the cross-section of the composition of this invention, and fi is the projected area of each of the particles.
- the effect of improving the adhesion strength of this invention tends to be reduced when the dipsersed particles of the polymer (B) has a [d] smaller than 0.1 micron or larger than 5 microns.
- the dispersed particles of the polymer (B) preferably should not be secondarily coagulated.
- the compatibility between the polymer (B) and the modified polyolefin (A) is especially important. If the compatibility is very good, the aforesaid dispersed state does not result.
- Such a polymer (B) in combination with the modified polyolefin (A) cannot form a good composition intended by the present invention. In selecting the polymer (B), therefore, its compatibility with the modified polyolefin (A) should be considered.
- Blending of the modified polyolefin (A) and the polymer (B) can be carried out by using polymer blending techniques known per se.
- the blending is carried out until the polymer (B) forms the aforesaid dispersed phase of particles in the modified polyolefin (A).
- the modified polyolefin (A) and the polymer (B) are kneaded at a temperature above the highest melting point of the two but below 350° C. by means of an extruder, a kneader, a two-roll mill, a Banbury mixer, etc.
- the individual components are mixed in the form of a solution or suspension, and the polymers are precipitated from the mixture, or the mixture is dried.
- the modified polyolefin is not directly obtained by copolymerization, but by after-modification of an olefin, for example by a grafting reaction, there can be used a method in which a mixture of the aforesaid base polyolefin and the polymer (B) may be used as the base polyolefin to be subjected to the modification reaction.
- This method is industrially advantageous because it makes possible both mixing of the polymer (B) and the production of the modified polyolefin (A).
- the polymer (B) might also be modified in this case, but so long as the modified product meets the requirement of the polymer (B), there is no problem.
- composition of this invention can consist essentially of the modified polyolefin (A) and the polymer (B). If desired, it may further contain additives such as antioxidants, ultraviolet absorbers, antistatic agents, pigments, dyes, nucleating agents, fillers, slip agents, fire retardants, plasticizers, etc. which are used in ordinary polymeric substances in amounts which do not adversely affect the advantages of this invention. It may also contain polymeric substances other than the modified polyolefin (A) and the polymer (B).
- the composition of this invention has especially good adhesion to polar substances as well as polyolefins, and can be advantageously used for producing laminates between the polar material and a polyolefin, or as an adhesive for bonding a plurality of polar substances.
- the polar substances include metals such as iron, copper, lead, nickel, zinc, and alloys of these metal elements such as stainless steel; concrete, wood, cellulose, natural fibers, and polar resins such as nylon, ethylene/vinyl alcohol copolymers, polyesters, polystyrene, polycarbonate, polyphenylene oxide, polyvinyl chloride, polyvinylidene chloride, polyacrylonitrile and ethylene/tetrafluoroethylene copolymer.
- the composition of this invention may be bonded to a polar material by heating both of them to render at least the composition of the invention molten and then bonding them to each other.
- the polar material is not thermoplastic
- the molten composition of this invention may be laminated to the polar material, or the two are superimposed in advance and then bonded under heat melting.
- the composition of this invention is adhered to the polar material by electrostatic charge and then melt-laminated.
- bonding can be effected by a method comprising melting both of the composition of this invention and the polar material and laminating them, or a method which comprises laminating the molten composition of the invention to the polar material.
- a method comprising melting both of the composition of this invention and the polar material and laminating them, or a method which comprises laminating the molten composition of the invention to the polar material.
- it is not necessary to subject one or both surfaces of the polar material to such treatments as flaming treatment, corona discharge treatment or coating of a primer. If desired, such a pre-treatment may be performed.
- composition of this invention usually has good adhesion to polyolefins, it can be advantageously used as an interlayer in producing a laminate of a polar material and a polyolefin.
- composition of this invention can be used in many applications, for example laminated films, laminated sheets, laminated bottles, rust-proof coatings of metal plates or pipes, hot-melt adhesives, paint film-forming elements.
- composition of this invention has improved adhesion to polar materials while retaining the other excellent properties of the modified polyolefin improved by modification.
- An ethylene/1-butene copolymer having a density of 0.930 g/cm 3 was kneaded with a styrene monomer and 2,5-dimethyl-2,5-di(tert.-butylperoxy)hexyne-3 in an extruder set at a temperature of 230° C. to prepare a styrene-grafted ethylene/1-butene copolymer (to be referred to as modified product A-1).
- the content of the styrene unit grafted was 1.7 ⁇ 10 -4 gram-equivalent/g.
- the modified product A-1 had an intrinsic viscosity of 1.18 dl/g and a crystallinity of 60%.
- composition (C-1) Ninety parts by weight of the modified product A-1 was mixed with 10 parts by weight of polyhexene-1 having a flexural modulus of less than 500 kg/cm 2 , a weight average molecular weight of 550,000 and a glass transition temperature of -50° C., and they were kneaded in an extruder set at a temperature of 230° C. to prepare a composition (C-1).
- a test sample having a width of 100 mm was cut off from the three-layer sheet, and the peel strength between the high-impact polystyrene layer and the composition C-1 layer and the peel strength between the medium-density polyolefin layer and the composition C-1 layer were measured.
- the peel strengths were measured by peeling the outer polymer layer (II) and the intermediate 100 micron thick polymer layer by 180 degrees at a rate of 50 mm/min. and a temperature of 23° C.
- a three-layer sheet was prepared in the same way as in Example 1 except that polyvinylidene chloride (Saran, a product of Dow Chemical Company) or polyethylene terephthalate (J145, a product of Toray Inc.) was used as the outside layer I instead of polystyrene, an acrylonitrile copolymer (BAREX, a product of Vistron Company) or polycarbonate (Panlite L-1250, a product of Teijin Chemical Co., Ltd.) was used as the outside layer II, and the manifold die was set at a temperature of 200° C. or 280° C.
- the peel strengths of the sheets are summarized in Table 1.
- a vinylmethoxysilane-grafted ethylene/1-butene copolymer was prepared in the same way as in Example 1 except that vinyltrimethoxysilane was used as the grafting monomer.
- the modified copolymer (to be referred to as modified product A-2) contained 0.88 ⁇ 10 -4 gram-equivalent/g of the vinyltrimethoxysilane unit, and had an intrinsic viscosity of 1.19 dl/g and a crystallinity of 59%.
- composition (C-2) Ninety parts by weight of the modified product A-2 was mixed with 10 parts by weight of the same polyhexene-1 as used in Example 1, and they were kneaded to prepare a composition (C-2).
- a three-layer sheet was prepared in the same way as in Example 1 except that polyvinylidene chloride, polyethylene terephthalate or polycarbonate used in Example 2 or 3 was used as the outside layer I, the manifold die was set at a temperature of 200 (Example 4), 280 (Example 5) or 280 (Example 6) °C., and the composition C-2 was used as the interlayer.
- Example 2 The same ethylene/1-butene copolymer as used in Example 1 was dissolved in p-xylene and subjected to grafting reaction at 125° C. using glycidyl methacrylate as a modifying monomer and dicumyl peroxide as an initiator. The reaction mixture was cooled to room temperature, and a large amount of acetone was added. The precipitate was collected by filtration. The precipitated polymer was repeatedly washed with acetone, and dried under vacuum.
- modified product A-3 contained 1.1 ⁇ 10 -4 gram-equivalent/g of the glycidyl methacrylate unit and had an intrinsic viscosity of 1.21 dl/g and a crystallinity of 58%.
- the modified product A-3 was mixed with 10% by weight of polyisobutylene having a flexural modulus of less than 500 kg/cm 2 , a weight average molecular weight of 650,000 and a glass transition temperature of -65° C., and they were kneaded to prepare a composition (C-3).
- a three-layer sheet was prepared in the same way as in Example 1 except that polyvinylidene chloride, polyethylene terephthalate, polycarbonate or acrylonitrile copolymer used in Example 2 or 3 or an ethylene/tetrafluoroethylene copolymer (AFLON, a product of Asahi Glass Co., Ltd.) was used as the outside layer I, the composition C-3 was used as the interlayer, and the manifold die was set at the same temperature as in Example 2 to 9 depending upon the kind of the outside layer I, or when the outside layer I was the ethylene/tetrafluoroethylene copolymer, the die was set at a temperature of 300° C.
- the peel strengths are summarized in Table 1.
- the same ethylene/1-butene copolymer as used in Example 1 was dissolved in chlorobenzene at 110° C., and chlorinated by blowing chlorine gas into the solution.
- the reaction mixture was cooled to room temperature.
- a large amount of methanol was added to precipitate the polymer.
- the precipitate was collected by filtration, repeatedy washed with methanol, and dried in vacuum to obtain a chlorinated ethylene/1-butene copolymer which had a chlorine content of 1.1 ⁇ 10 -3 gram-equivalent/g, an intrinsic viscosity of 1.12 dl/g and a crystallinity of 48% (the chlorinated polymer is referred to as modified product A-4).
- the modified product A-4 was kneaded with 10% by weight of the same polyisobutylene as used in Example 7 and 1% by weight of epoxidized soybean oil to form a composition (C-4).
- a three-layer sheet was prepared in the same way as in Example 1 except that the polystyrene, polyvinylidene chloride, polyethylene terephthalate or polycarbonate used in Examples 1 to 11 was used as the outside layer I, the manifold die was set at the same temperatures as in Examples 1 to 11 depending upon the kind of the outside layer I, and the composition C-4 was used as the interlayer.
- the three-layer sheets shown in Table 2 were prepared in the same way as in Example 1 using the compositions or outside layer polymers shown in Table 2. The properties of the sheets are shown in Table 2.
- the three-layer sheets shown in Table 3 were prepared in the same way as in Example 1 using the compositions or outside layer polymers shown in Table 3. The properties of the sheets are shown in Table 3.
- compositions shown in Table 4 were prepared by using the ethylene copolymers indicated in Table 4 as a polyolefin having a polar group, and by laminating the resulting compositions and the outside layer polymers shown in Table 4, three-layer sheets were prepared.
- compositions C-3 and C-6 used in Examples 7 and 17 and the composition C-24 used in Comparative Example 11 were used as an adhesive layer.
- two-layer co-extrusion coating was carried out on a 1-inch steel pipe (JIS No. SGP) which had been degreased and pickled.
- the thickness of the adhesive layer was 100 microns and the thickness of high-density polystyrene (Hizex 5100E, a product of Mitsui Petrochemical Industries, Ltd.) on it was adjusted to 2 mm.
- the temperature at which the steel pipe was preheated was 200° C., and the temperature of the extruded resins was 230° C.
- the coated pipe was cooled with water, and a test sample having a width of 10 mm was cut off from it.
- the peel strength between the steel and the composition layer was measured at a peeling angle of 90°.
- the delamination strength was 17, 16 and 5 kg/cm, respectively.
- the overcoated high-density polyethylene could not be peeled from the adhesive layer.
- composition C-34 in which the dispersed particles had an average diameter of 1 to 3 microns was prepared in the same way as in Example 1 except that 10% by weight of polypropylene (flexural modulus 15000 kg/cm 2 , the adhesion strength with respect to the modified product A-1 250 g/cm) was added instead of polyhexene-1 to the modified product A-1.
- polypropylene flexural modulus 15000 kg/cm 2 , the adhesion strength with respect to the modified product A-1 250 g/cm
- a laminate with high-impact polystyrene was prepared in the same way as in Example 1 except that the composition C-34 was used as an interlayer.
- the peel strength between the interlayer and the outer layer I was 580 g/cm, and the outerlayer II (medium-density polyethylene) could not be peeled from the interlayer.
Abstract
Description
______________________________________ Blending proportions (parts by weiqht) Broadest Preferred Most preferred possible range range range ______________________________________ Modified 50-99 60-97 70-95 polyolefin (A) Polymer (B) 50-1 40-3 30-5 ______________________________________
TABLE 1 Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Composition used as the interlayer Modified polyolefin (A) Modified product No. A-1 A-1 A-1 A-2 A-2 A-2 Base polyolefin Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene copolymer copolymer copolymer copolymer copolymer copolymer Density (g/cc) of the base polyolefin 0.930 0.930 0.930 0.930 0.930 0.930 Modifier Styrene Styrene Styrene Vinyltrimethoxysilane Vinyltrimethoxysilane Vinyltrimethoxysilane Content (g-equivalent/g) of the modifier 1.7 × 10.sup.-4 1.7 × 10.sup.-4 1.7 × 10.sup.-4 0.88 × 10.sup.-4 0.88 × 10.sup.-4 0.88 × 10.sup.-4 [η] (dl/g) 1.18 1.18 1.18 1.19 1.19 1.19 Crystallinity (%) 60 60 60 59 59 59 --Mw/--Mn 8.2 8.2 8.2 8.5 8.5 8.5 Polymer (B) Name Polyhexene-1 Polyhexene-1 Polyhexene-1 Polyhexene-1 Polyhexene-1 Polyhexene-1 Type Elastomer (soft) Elastomer (soft) Elastomer (soft) Elastomer (soft) Elastomer (soft) Elastomer (soft) --Mw 550,000 550,000 550,000 550,000 550,000 550,000 Tg (° C.) -50 -50 -50 -50 -50 -50 Flexural modulus (kg/cm.sup.2) less than 500 less than 500 less than 500 less than 500 less than 500 less than 500 Strength of adhesion to the -- -- -- -- -- -- modified product (g/cm) Method of addition After-blending After-blending After-blending After-blending After-blending After-blending Amount added (% by weight) 10 10 10 10 10 10 --Mw/--Mn 5.8 5.8 5.8 5.8 5.8 5.8 Crystallinity (%) 0 0 0 0 0 0 C omposition No. C-1 C-1 C-1 C-2 C-2 C-2 Average diameter of the 1-2 1-2 1-2 1-2 1-2 1-2 dispersed particles (microns) Three-layer sheet Polymer of the outside layer I High-impact Polyvinylidene Polyethylene Polyvinyli dene Polyethylene Polycarbonate polystyrene chloride terephthalate chloride terephthalate Polymer of the outside layer II Medium-density Acrylonitrile Polycarbonate Medium-density Medium-density Medium-density polyethylene copolymer polyethylene polyethylene polyethylene Peel strength with respect to the 1100 1050 980 520 610 1000 outside layer I (g/cm) Peel strength with respect to the Peeling impossible 900 1100 Peeling impossible Peeling impossible Peeling impossible outside layer II (g/cm) Example 7 Example 8 Example 9 Example 10 Example 11 Composition used as the interlayer Modified polyolefin (A) Modified product No. A-3 A-3 A-3 A-3 A-3 Base polyolefin Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene copolymer copolymer copolymer copolymer copolymer Density (g/cc) of the base polyolefin 0.930 0.930 0.930 0.930 0.930 Modifier Glycidyl Glycidyl Glycidyl Glycidyl Glycidyl methacrylate methacrylate methacrylate methacrylate methacrylate Content (g-equivalent/g) of the modifier 1.1 × 10.sup.-4 1.1 × 10.sup.-4 1.1 × 10.sup.-4 1.1 × 10.sup.-4 1.1 × 10.sup.-4 [η] (dl/g) 1.21 1.21 1.21 1.21 1.21 Crystallinity (%) 58 58 58 58 58 --Mw/--Mn 7.2 7.2 7.2 7.2 7.2 Polymer (B) Name Polyisobutylene Polyisobutylene Polyisobutylene Polyisobutylene Polyisobutylene Type Elastomer (soft) Elastomer (soft) Elastomer (soft) Elastomer (soft) Elastomer (soft) --Mw 650,000 650,000 650,000 650,000 650,000 Tg (°C.) -63 -63 -63 - 63 -63 Flexural modulus (kg/cm.sup.2) less than 500 less than 500 less than 500 less than 500 less than 500 Strength of adhesion to the -- -- -- -- -- modified product (g/cm) Method of addition After-blending After-blending After-blending After-blending After-blending Amount added (% by weight) 10 10 10 10 10 --Mw/--Mn 4.9 4.9 4.9 4.9 4.9 Crystallinity (%) 0 0 0 0 0 Composition No. C-3 C-3 C-3 C-3 C-3 Average diameter of the 1-2 1-2 1-2 1-2 1-2 dispersed particles (microns) Three-layer sheet Polymer of the outside layer I Polyvinylidene Polyethylene Polycarbonate Acrylonitri le Ethylene/tetrafluoro- chloride terephthalate copolymer ethylene copolymer Polymer of the outside layer II Medium-density Medium-density Medium-density Medium-density Medium-density polyethylene polyethylene polyethylene polyethylene polyethylene Peel strength with respect to the 980 1200 1500 1800 1200 outside layer I (g/cm) Peel strength with respect to the Peeling impossible Peeling impossible Peeling impossible Peeling impossible Peeling impossible outside layer II (g/cm)
TABLE 2 Example 12 Example 13 Example 14 Example 15 Example 16 Example 17 Example 18 Composition used as the interlayer Modified polyolefin (A) Modified product No. A-4 A-4 A-4 A-4 A-1 A-3 A-1 Base polyolefin Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene copolymer copolymer copolymer copolymer copolymer copolymer copolymer Density (g/cc) of the base polyolefin 0.930 0.930 0.930 0.930 0.930 0.930 0.930 Modifier Chlorine gas Chlorine gas Chlorine gas Chlorine gas Styrene Glycidyl Styrene methacrylate Content (g-equivalent/g) of the modifier 3.9 × 10.sup.-3 3.9 × 10.sup.-3 3.9 × 10.sup.-3 3.9 × 10.sup.-3 1.7 × 10.sup.-4 1.1 × 10.sup.-4 1.7 × 10.sup.-4 [η] (dl/g) 1.12 1.12 1.12 1.12 1.18 1.21 1.18 Crystallinity (%) 48 48 48 48 60 58 50 --Mw/--Mn 7.3 7.3 7.3 7.3 8.2 7.2 8.2 Polymer (B) Name Polyisobutylene Polyisobutylene Polyisobutylene Polyisobutylene Nylon 6 Polystyrene Polyisobutylene** Type Elastomer (soft) Elastomer (soft) Elastomer (soft) Elastomer (soft) Plastic (hard) Plastic (hard) Elastomer (soft) --Mw 650,000 650,000 650,000 650,000 -- -- 800,000 Tg (°C.) -63 -63 -63 -63 -- -- -65 Flexural modulus (kg/cm.sup.2) less than 500 less than 500 less than 500 less than 500 22,000 37,000 less than 500 Strength of adhesion to the -- -- -- -- 20 20 -- modified product (g/cm) Method of addition After-blending After-ble nding After-blending After-blending After-blending After-blending Blending before modification Amount added (% by weight) 10 10 10 10 10 10 10 --Mw/--Mn 4.9 4.9 4.9 4.9 -- -- 5.2 Crystallinity (%) 0 0 0 0 -- -- 0 Composition No. C-4 C-4 C-4 C-4 C-5 C-6 C-7 Average diameter of the 2 2 2 2 5 1-3 1-3 dispersed particles (microns) Three-layer sheet Polymer of the outside layer I High-impact Polyvinylide ne Polyethylene Polycarbonate Polyethylene Acrylonitrile High-impact polystyrene chloride terephthalate terephthalate copolymer polystyrene Polymer of the outside layer II Medium-density Medium-density Medium density Medium-density Medium-density Medium-density Medium-density polyethylene polyethylene polyethylene polyethylene polyethylene polyethylene polyethylene Peel strength with respect to the 1500 1900 1080 2150 880 1600 1050 outside layer I (g/cm) Peel strength with respect to the Peeling impossible Peeling impossible Peeling impossible Peeling impossible Peeling impossible Peeling impossible Peeling impossible outside layer II (g/cm) Example 19 Example 20 Example 21 Example 22 Example 23 Example 24 Example 25 Composition used as the interlayer Modified polyolefin (A) Modified product No. A-5 A-6 A-7 A-8 A-9 A-10 A-1 Base polyolefin Polypropylene Poly(4-methyl-1- Ethylene/4-methyl- Ethylene/1-butene Polypropylene Polypropylene Ethylene/1-butene pentene) 1-pentene copolymer copolymer copolymer Density (g/cc) of the base polyolefin 0.91 0.83 0.950 0.90 0.91 0.91 0.930 Modifier Styrene Styrene Styrene Styrene Styrene Styrene Styrene Content (g-equivalent/g) of the modifier 2.2 × 10.sup.-4 2.4 × 10.sup.-4 1.8 × 10.sup.-4 2.4 × 10.sup.-4 2.2 × 10.sup.-4 2.2 × 10.sup.-4 1.7 × 10.sup.-4 [ η] (dl/g) 1.48 1.12 1.61 2.52 1.48 1.48 1.18 Crystallinity (%) 55 35 52 25 55 55 60 --Mw/--Mn 6.8 7.3 6.9 3.8 6.8 6.8 8.2 Polymer (B) Name Polyhexene-1 Polyisobutylene Polyisobutylene Polyisobutylene Polyhexene-1 Low-density Ethylene/propylene copolymer Type Elastomer (soft) Elastomer (soft) Elastomer (soft) Elastomer (soft) Elastomer (soft) Plastic (hard) Elastomer (soft) --Mw 1,000,000 450,000 450,000 450,000 550,000 2500 450,000 Tg (°C.) -50 -60 -65 -65 -50 -- -44 Flexural modulus (kg/cm.sup.2) less than 500 less than 500 less than 500 less than 500 less than 500 1500 less than 500 Strength of adhesion to the -- -- -- -- -- 40 -- modified product (g/cm) Method of addition After-blending After-blending After-blending After-blending After-blending After-blending After-blending Amount added (% by weight) 10 -- 10 5 30 10 10 --Mw/--Mn 6.3 5.2 5.2 5.2 5.8 -- 4.2 Crystallinity (%) 0 0 0 0 0 -- 15 Composition No. C-8 C-9 C-10 C-11 C-12 C-13 C-14 Average diameter of the 2-4 0.5-2 2-4 0.5-2 0.5-4 0.5-2 0.15 dispersed particles (microns) Three-layer sheet Polymer of the outside layer I Polyvinylidene Polycarbonate Polyethylene Polyethylene Polycarbonate Polyvinylidene Polyethylene chloride terephthalate terephthalate chloride terephthalate Polymer of the outside layer II Polypropylene Poly(4-methyl-1- Medium-density Medium-density Polypropylene Polypropylen e Polycarbonate pentene) polyethylene polyethylene Peel strength with respect to the 900 810 880 980 800 820 830 outside layer I (g/cm) Peel strength with respect to the Peeling impossible Peeling impossible Peeling impossible Peeling impossible Peeling impossible Peeling impossible 900 outside layer II (g/cm) **Partly containing a styrenegrafted product
TABLE 3 Comparative Comparative Comparative Comparative Comparative Comparative Comparative Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Composition used as the interlayer Modified polyolefin (A) Modified product No. A-1 A-1 A-1 A-1 A-1 A-1 A-1 Base polyolefin Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene copolymer copolymer copolymer copolymer copolymer copolymer copolymer Density (g/cc) of the base polyolefin 0.930 0.930 0.930 0.930 0.930 0.930 0.930 Modifier Styrene Styrene Styrene Styrene Styrene Styrene Styrene Content (g-equivalent/g) of the modifier 1.7 × 10.sup.-4 1.7 × 10.sup.-4 1.7 × 10.sup.-4 1.7 × 10.sup.-4 1.7 × 10.sup.-4 1.7 × 10.sup.-4 1.7 × 10.sup.-4 [η] (dl/g) 1.18 1.18 1.18 1.18 1.18 1.18 1.18 Crystallinity (%) 60 60 60 60 60 60 60 --Mw/--Mn 8.2 8.2 8.2 8.2 8.2 8.2 8.2 Polymer (B) Name -- -- -- Polyhexene-1 Polyhexene-1 Polystyrene Ethylene/propylene copolymer Type -- -- -- Elastomer (soft) Elastomer (soft) Plastic (hard) Elastomer --Mw -- -- -- 100,000 100,000 -- 200,000 Tg (°C.) -- -- -- -50 -50 -- -45 Flexural modulus (kg/cm.sup.2) -- -- -- less than 500 less than 500 22,000 less than 500 Strength of adhesion to the -- -- -- -- -- 350 -- modified product (g/cm) Method of addition -- -- -- After-blending After-blending After-blending After-blending Amount added (% by weight) -- -- -- 10 7.0 10 10 --Mw/--Mn -- -- -- 4.6 4.6 -- 3.8 Crystallinity (%) -- -- -- 0 0 -- 15 Composition No. C-15 C-16 C-16 C-17 C-18 C-19 C-20 Average diameter of the -- -- -- 0.5-1 5-10 0.5-2 less than 0.1 dispersed particles (microns) Three-layer sheet Polymer of the outside layer I High-impact Polyvinylidene Polyethylene Polyethylene Polyethylene Polyethylene Polyethylene polystyrene chloride terephthalate terephthal ate terephthalate terephthalate terephthalate Polymer of the outside layer II Medium-density Acrylonitrile Polycarbonate Polycarbonate Polycarbonate Polycarbonate Polycarbonate polyethylene copolymer Peel strength with respect to the 400 410 380 420 370 400 420 outside layer I (g/cm) Peel strength with respect to the Peeling impossible 300 410 410 700 Peeling impossible Peeling impossible outside layer II (g/cm) Comparative Comparative Comparative Comparative Comparative Comparativ e Comparative Example 8 Example 9 Example 10 Example 11 Example 12 Example 13 Example 14 Composition used as the interlayer Modified polyolefin (A) Modified product No. A-10 A-10 A-2 A-3 A-4 A-5 A-1 Base polyolefin Ethylene/1-bute ne Ethylene/1-butene Ethylene/1-butene Ethylene/1-butene Ethylene/1-buten e Polypropylene Ethylene/1-butene copolymer copolymer copolymer copolymer copolymer copolymer Density (g/cc) of the base polyolefin 0.88 0.88 0.930 0.930 0.930 0.91 0.930 Modifier Styrene Styrene Vinyltrim ethoxy- Glycidyl Chlorine gas Styrene Styrene silane methacrylate Content (g-equivalent/g) of the modifier 1.8 × 10.sup.-4 1.8 × 10.sup.-4 0.88 × 10.sup.-4 1.1 × 10.sup.-4 3.9 × 10.sup.-3 2.2 × 10.sup.-4 1.7 × 10.sup.-4 [η] (dl/g) 1.45 1.45 1.19 1.21 1.12 1.48 1.18 Crystallinity (%) 13 13 59 58 52 55 60 --Mw/--Mn 3.5 3.5 8.5 7.2 7.3 6.8 8.2 Polymer (B) Name Polyisobutylene -- -- -- -- -- Ethylene/1-butene copolymer Type Elastomer (soft) -- -- -- -- -- Plastic (hard) --Mw 600,000 -- -- -- -- -- -- Tg (°C.) -65 -- -- -- -- -- -- Flexural modulus (kg/cm.sup.2) less than 500 -- -- -- -- -- 2500 Strength of adhesion to the -- -- -- -- -- -- 1000 modified product (g/cm) Method of addition After-blending -- -- -- -- -- After-blending Amount added (% by weight) 10 -- -- -- -- -- 10 --Mw/--Mn 5.3 -- -- -- -- -- -- Crystallinity (%) 0 -- -- -- -- -- -- Composition No. C-21 C-22 C-23 C-24 C-25 C-26 C-27 Average diameter of the 0.5-2 -- -- -- -- -- 0.1-0.5 dispersed particles (microns) Three-layer sheet Polymer of the outside layer I High-impact High-impact Polyvinylidene Polyvinylidene High-impact Polyvinylidene High-impact polystyrene polystyrene chloride chloride polystyrene chloride polystyrene Polymer of the outside layer II Medium-density Medium-density Medium-density Medium-density Medium-density Polypropylene Medium-density polyethylene polyethylene polyethylene polystyrene polystyrene polystyrene Peel strength with respect to the 550 550 250 300 580 300 410 outside layer I (g/cm) Peel strength with respect to the Peeling impossible Peeling impossible Peeling impossible Peeling impossible Peeling impossible Peeling impossible Peeling impossible outside layer II (g/cm)
TABLE 4 __________________________________________________________________________ Comparative Comparative Comparative Example 26 Example 15 Example 27 Example 16 Example 28 Example __________________________________________________________________________ 17 Composition used as the interlayer Polar group-containing ethylene copolymer (A) Polar monomer 1 Glycidyl Glycidyl Vinyl acetate Vinyl chloride Vinyl acetate Vinyl chloride methacrylate methacrylate Content (g-equivalent/g) 2.7 × 10.sup.-4 2.7 × 10.sup.-4 1.7 × 10.sup.-3 1.7 × 10.sup.-3 1.4 × 10.sup.-3 1.4 × 10.sup.-3 of polar monomer 1 Polar monomer 2 Ethyl acrylate Ethyl acrylate None None Vinyl alcohol Vinyl alcohol Content (g-equivalent/g) 5.0 × 10.sup.-4 5.0 × 10.sup.-4 -- -- 1.4 × 10.sup.-3 1.4 × 10.sup.-3 of polar monomer 2 [η] (dl/g) 1.43 1.43 1.03 1.03 0.85 0.85 Crystallinity (%) 50 50 40 40 25 25 --Mw/--Mn 16 16 16 16 18 18 Polymer (B) Name Polyisoprene -- Polyisobutylene -- Polyisobutylene -- Type Elastomer (soft) -- Elastomer (soft) -- Elastomer --oft) --Mw 800,000 -- 800,000 -- 800,000 -- Tg (°C.) -65 -- -65 -- -65 -- Flexural modulus (kg/cm.sup.2) less than 500 -- less than 500 -- less than --0 Strength of adhesion to the -- -- -- -- -- -- above copolymer (g/cm) Method of addition After-blending -- After-blending -- After-blending -- Amount added (% by weight) 10 -- 10 -- 10 -- --Mw/--Mn 5.2 -- 5.2 -- 5.2 -- Crystallinity (%) 0 -- 0 -- 0 -- Composition No. C-28 C-31 C-29 C-32 C-30 C-33 Average diameter of the 0.5-2 -- 0.5-2 -- 1-2 -- dispersed particles (microns) Three-layer sheet Polymer of the outside layer I Polyethylene Polyethylene Polyvinylidene Polyvinylidene Polyethylene Polyethylene terephthalate terephthalate chloride chloride terephthalate terephthalate Polymer of the outside layer II Polyvinylidene Polyvinylidene High-impact High-impact Ethylene/vinyl Ethylene/vinyl chloride chloride polystyrene polystyrene alcohol alcohol copolymer copolymer Peel strength with respect to 1300 400 1100 500 1760 500 the outside layer I (g/cm) Peel strength with respect to 1190 410 800 200 750 190 the outside layer II (g/cm) __________________________________________________________________________
Claims (17)
Applications Claiming Priority (2)
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JP58171183A JPS6063243A (en) | 1983-09-19 | 1983-09-19 | Highly adhesive composition |
JP58-171183 | 1983-09-19 |
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US4632959A true US4632959A (en) | 1986-12-30 |
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US06/651,894 Expired - Lifetime US4632959A (en) | 1983-09-19 | 1984-09-19 | Modified polyolefin composition |
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US (1) | US4632959A (en) |
EP (1) | EP0140121B1 (en) |
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WO1987007900A1 (en) * | 1986-06-17 | 1987-12-30 | Mitsui Petrochemical Industries, Ltd. | Epoxy resin composition and process for preparing the same |
JPH0759313B2 (en) * | 1987-10-20 | 1995-06-28 | 東レ株式会社 | Binder composition for flocking of polyolefin molded products |
JP2509398B2 (en) * | 1991-06-14 | 1996-06-19 | 昭和電工株式会社 | Container made of laminated body |
AU2003207187A1 (en) * | 2002-02-08 | 2003-09-02 | Oji Paper Co., Ltd. | Rust preventive film for stretch packaging |
JP5290692B2 (en) * | 2008-10-08 | 2013-09-18 | 株式会社カネカ | Laminated body |
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US4483965A (en) * | 1979-10-09 | 1984-11-20 | Mitsubishi Petrochemical Co., Ltd. | Stretched film |
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US3695922A (en) * | 1969-04-17 | 1972-10-03 | Diacel Ltd | Coated polyolefin films and process for preparing same |
US3987122A (en) * | 1972-04-03 | 1976-10-19 | Exxon Research And Engineering Company | Thermoplastic adhesive compositions |
JPS54113629A (en) * | 1978-02-25 | 1979-09-05 | Gunze Kk | Coating composition |
CA1157990A (en) * | 1979-03-08 | 1983-11-29 | Hisaya Sakurai | Thermoplastic resinous composition |
US4320421A (en) * | 1980-05-27 | 1982-03-16 | International Business Machines Corporation | Rotary actuator for file protect function |
DE3371914D1 (en) * | 1982-07-16 | 1987-07-09 | Mitsui Petrochemical Ind | Hot-melt adhesive composition |
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1983
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1984
- 1984-09-17 EP EP84111077A patent/EP0140121B1/en not_active Expired - Lifetime
- 1984-09-17 DE DE3486302T patent/DE3486302T2/en not_active Expired - Lifetime
- 1984-09-19 US US06/651,894 patent/US4632959A/en not_active Expired - Lifetime
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US4483965A (en) * | 1979-10-09 | 1984-11-20 | Mitsubishi Petrochemical Co., Ltd. | Stretched film |
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US4937284A (en) * | 1983-02-17 | 1990-06-26 | Neste Oy | Modified polyolefin, method for making the same, and use thereof |
US4761452A (en) * | 1985-07-12 | 1988-08-02 | Shin-Etsu Chemical Co., Ltd. | Oil-resistant rubber composition |
US4959405A (en) * | 1986-06-04 | 1990-09-25 | Illinois Tool Works, Inc. | Acid modified adhesive composition |
US4845157A (en) * | 1986-12-29 | 1989-07-04 | Texaco Inc. | Diesel fuel compositions containing polyolefin graft polymers |
US5077123A (en) * | 1987-05-28 | 1991-12-31 | Mitsui Petrochemical Industries, Ltd. | Laminated film having poly(4-methyl-1-penetene) base layer |
US5069927A (en) * | 1989-03-03 | 1991-12-03 | Bridgestone/Firestone, Inc. | Adhesively-bonded coated composites of highly saturated elastomers |
US5134194A (en) * | 1990-01-24 | 1992-07-28 | Mitsubishi Petrochemical Co., Ltd. | Thermoplastic resin composition |
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US5648126A (en) * | 1992-06-12 | 1997-07-15 | Taiyo Steel Co., Ltd. | Process for manufacturing a surface-treated metal sheet of high durability |
US5272195A (en) * | 1992-07-14 | 1993-12-21 | Phillips Petroleum Company | Glass-reinforced chemically coupled branched higher alpha-olefin compounds |
US5588468A (en) * | 1993-12-23 | 1996-12-31 | Ems-Inventa Ag | Blow-molded coolant conduit |
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US20100276057A1 (en) * | 2009-04-30 | 2010-11-04 | H.B. Fuller Company | Ethylene-butene copolymer, adhesive composition including the same, and method of making and using the same |
US9150004B2 (en) | 2009-06-19 | 2015-10-06 | Toray Plastics (America), Inc. | Biaxially oriented polylactic acid film with improved heat seal properties |
US8734933B2 (en) | 2009-09-25 | 2014-05-27 | Toray Plastics (America), Inc. | Multi-layer high moisture barrier polylactic acid film |
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US10619081B2 (en) | 2017-05-22 | 2020-04-14 | H.B. Fuller Company | Hot melt adhesive composition |
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Also Published As
Publication number | Publication date |
---|---|
JPH0420939B2 (en) | 1992-04-07 |
JPS6063243A (en) | 1985-04-11 |
EP0140121A3 (en) | 1988-06-22 |
DE3486302D1 (en) | 1994-05-19 |
EP0140121A2 (en) | 1985-05-08 |
DE3486302T2 (en) | 1994-09-01 |
EP0140121B1 (en) | 1994-04-13 |
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